After 30 years inside corporate travel, the last thing I expected to start was a retreat planning practice. But the gap between what distributed teams need and what existing platforms deliver is wider than the industry admits.
I served as senior VIP travel advisor to UPS for five years, built and led the global meetings function for The Nature Conservancy for eight, and managed executive engagements for Coca-Cola, Tyler Perry Studios, and other Fortune 100 brands.
The 30-year version
I was the person on the other end of the phone when a flight got cancelled at 3am. I knew which visa office to call on a Sunday, which hotel general manager owed me a favour. Those are skills you build only by being in the seat for years while real money and real careers depend on the trip happening on schedule.
What changed
COVID hit and the entire corporate travel category broke. When trips came back, they came back different. Distributed work meant companies didn’t have headquarters anymore. What didn’t change: most retreat platforms still operate like budget travel agencies, optimised for filling rooms, not for designing experiences that actually deliver.
Why I started Trip Happens
The blog was the start. The Fora Travel advisor credential came next. Then founders and People Ops leads started asking, “We’re doing an offsite in October. Can you help?” They wanted someone who’d been on the other side of complex international travel logistics.
What changed between 2019 and now isn’t the kind of travel companies do, it’s who plans it.
What I actually do
Discovery and design, venue selection with partner programme perks (Virtuoso, Four Seasons Preferred Partner, Hyatt Prive, Marriott STARS, Belmond Bellini Club), contract negotiation, and pre-trip packets with on-trip support.
Who this is for
Founders of 10 to 100 person distributed companies, People Ops leads, Chief of Staff at remote-first companies, and teams whose last offsite was “fine” but expensive.
The start is a free 30-minute intake call. No commitment, no pressure, no upsell.